C–H 18F-fluorination of 8-methylquinolines with Ag[18F]F

Lee, So Jeong; Brooks, Allen F.; Ichiishi, Naoko; Makaravage, Katarina J.; Mossine, Andrew V.; Sanford, Melanie S.; Scott, Peter J. H.

doi:10.1039/c9cc00641a

Title: C–H ¹⁸F-fluorination of 8-methylquinolines with Ag[¹⁸F]F

Journal Article · 11 February 2019 · ChemComm

DOI: https://doi.org/10.1039/c9cc00641a · OSTI ID:1611829

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Univ. of Michigan, Ann Arbor, MI (United States). Dept. of Radiology; DOE/OSTI
Univ. of Michigan, Ann Arbor, MI (United States). Dept. of Radiology
Univ. of Michigan, Ann Arbor, MI (United States). Dept. of Chemistry

This report describes a Pd-mediated C–H radiofluorination of 8-methylquinoline derivatives with no-carrier-added Ag[¹⁸F]F. To achieve this transformation, a new method was developed for the generation of Ag[¹⁸F]F using a sep-pak cartridge. The C–H radiofluorination was then optimized and applied to a series of substituted 8-methylquinoline derivatives. Finally, this method was fully automated using a radiochemistry synthesis module.

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Research Organization:: Univ. of Michigan, Ann Arbor, MI (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Biological and Environmental Research (BER)

Grant/Contract Number:: SC0012484

OSTI ID:: 1611829

Journal Information:: ChemComm, Journal Name: ChemComm Journal Issue: 20 Vol. 55; ISSN 1359-7345

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

References (29)

Synthesis of Arylated Quinolines by Chemo- and Site-selective Suzuki-Miyaura Reactions of 5,7-Dibromo-8-(trifluoromethanesulfonyloxy)quinoline Eleya, Nadi; Mahal, Ahmed; Hein, Martin Advanced Synthesis & Catalysis, Vol. 353, Issue 14-15 https://doi.org/10.1002/adsc.201100165	journal	September 2011
Synthesis of ¹¹ C, ¹⁸ F, ¹⁵ O, and ¹³ N Radiolabels for Positron Emission Tomography Miller, Philip W.; Long, Nicholas J.; Vilar, Ramon Angewandte Chemie International Edition, Vol. 47, Issue 47 https://doi.org/10.1002/anie.200800222	journal	November 2008
¹⁸ F Labeling of Arenes Tredwell, Matthew; Gouverneur, Véronique Angewandte Chemie International Edition, Vol. 51, Issue 46 https://doi.org/10.1002/anie.201204687	journal	October 2012
Late-Stage Fluorination: Fancy Novelty or Useful Tool? Neumann, Constanze N.; Ritter, Tobias Angewandte Chemie International Edition, Vol. 54, Issue 11 https://doi.org/10.1002/anie.201410288	journal	February 2015
Targeted Fluorination with the Fluoride Ion by Manganese-Catalyzed Decarboxylation Huang, Xiongyi; Liu, Wei; Hooker, Jacob M. Angewandte Chemie International Edition, Vol. 54, Issue 17 https://doi.org/10.1002/anie.201500399	journal	March 2015
Inside Cover: Ultra-Tuning of the Aperture Size in Stiffened ZIF-8_Cm Frameworks with Mixed-Linker Strategy for Enhanced CO ₂ /CH ₄ Separation (Angew. Chem. Int. Ed. 1/2019) Hou, Qianqian; Wu, Ying; Zhou, Sheng Angewandte Chemie International Edition, Vol. 58, Issue 1 https://doi.org/10.1002/anie.201813331	journal	December 2018
Chemistry with [18F]Fluoride Ion Cai, Lisheng; Lu, Shuiyu; Pike, Victor W. European Journal of Organic Chemistry, Vol. 2008, Issue 17 https://doi.org/10.1002/ejoc.200800114	journal	June 2008
18F-labeled lower fluoroalkanes; Reactor-produced gaseous physiological tracers Gatley, S. J.; Hichwa, R. D.; Shaughnessy, W. J. The International Journal of Applied Radiation and Isotopes, Vol. 32, Issue 4 https://doi.org/10.1016/0020-708X(81)90051-X	journal	April 1981
Silver oxide assisted synthesis of fluoroalkanes; Measurements with a fluoride electrode and with fluorine-18 Gatley, S. John The International Journal of Applied Radiation and Isotopes, Vol. 33, Issue 4 https://doi.org/10.1016/0020-708X(82)90023-0	journal	April 1982
Semiautomated synthesis of a novel [18F] amine fluorocyanoborane for PET imaging studies. Radiosynthesis and in vivo characterization in rats Shalom, Eli; Takrouri, Khuloud; Metsuyanim, Nir Applied Radiation and Isotopes, Vol. 65, Issue 2 https://doi.org/10.1016/j.apradiso.2006.08.014	journal	February 2007
¹⁸ F-Labeling of Arenes and Heteroarenes for Applications in Positron Emission Tomography Preshlock, Sean; Tredwell, Matthew; Gouverneur, Véronique Chemical Reviews, Vol. 116, Issue 2 https://doi.org/10.1021/acs.chemrev.5b00493	journal	January 2016
PET Neuroimaging Studies of [ ¹⁸ F]CABS13 in a Double Transgenic Mouse Model of Alzheimer’s Disease and Nonhuman Primates Liang, Steven H.; Holland, Jason P.; Stephenson, Nickeisha A. ACS Chemical Neuroscience, Vol. 6, Issue 4 https://doi.org/10.1021/acschemneuro.5b00055	journal	March 2015
Fluorine-18 Radiochemistry, Labeling Strategies and Synthetic Routes Jacobson, Orit; Kiesewetter, Dale O.; Chen, Xiaoyuan Bioconjugate Chemistry, Vol. 26, Issue 1 https://doi.org/10.1021/bc500475e	journal	December 2014
Molecular Imaging with PET Ametamey, Simon M.; Honer, Michael; Schubiger, Pius August Chemical Reviews, Vol. 108, Issue 5 https://doi.org/10.1021/cr0782426	journal	May 2008
Palladium-Catalyzed Asymmetric Synthesis of Allylic Fluorides Katcher, Matthew H.; Doyle, Abigail G. Journal of the American Chemical Society, Vol. 132, Issue 49 https://doi.org/10.1021/ja109120n	journal	December 2010
Copper-Mediated Fluorination of Aryl Iodides Fier, Patrick S.; Hartwig, John F. Journal of the American Chemical Society, Vol. 134, Issue 26 https://doi.org/10.1021/ja304410x	journal	June 2012
Copper-Catalyzed, Directing Group-Assisted Fluorination of Arene and Heteroarene C–H Bonds Truong, Thanh; Klimovica, Kristine; Daugulis, Olafs Journal of the American Chemical Society, Vol. 135, Issue 25 https://doi.org/10.1021/ja4047125	journal	June 2013
Late Stage Benzylic C–H Fluorination with [ ¹⁸ F]Fluoride for PET Imaging Huang, Xiongyi; Liu, Wei; Ren, Hong Journal of the American Chemical Society, Vol. 136, Issue 19 https://doi.org/10.1021/ja5039819	journal	May 2014
Palladium-Catalyzed Intramolecular Aminofluorination of Unactivated Alkenes Wu, Tao; Yin, Guoyin; Liu, Guosheng Journal of the American Chemical Society, Vol. 131, Issue 45 https://doi.org/10.1021/ja9076588	journal	November 2009
Pd-Catalyzed C–H Fluorination with Nucleophilic Fluoride McMurtrey, Kate B.; Racowski, Joy M.; Sanford, Melanie S. Organic Letters, Vol. 14, Issue 16 https://doi.org/10.1021/ol301739f	journal	July 2012
Silver-Catalyzed Vinylogous Fluorination of Vinyl Diazoacetates Qin, Changming; Davies, Huw M. L. Organic Letters, Vol. 15, Issue 24 https://doi.org/10.1021/ol403017e	journal	November 2013
Development of Customized [18F]Fluoride Elution Techniques for the Enhancement of Copper-Mediated Late-Stage Radiofluorination Mossine, Andrew V.; Brooks, Allen F.; Ichiishi, Naoko Scientific Reports, Vol. 7, Issue 1 https://doi.org/10.1038/s41598-017-00110-1	journal	March 2017
Late-stage [ ¹⁸ F]fluorination: new solutions to old problems Brooks, Allen F.; Topczewski, Joseph J.; Ichiishi, Naoko Chem. Sci., Vol. 5, Issue 12 https://doi.org/10.1039/C4SC02099E	journal	January 2014
ONO pincer type Pd( ii ) complexes: synthesis, crystal structure and catalytic activity towards C-2 arylation of quinoline scaffolds Arumugam, Vignesh; Kaminsky, Werner; Nallasamy, Dharmaraj RSC Advances, Vol. 5, Issue 95 https://doi.org/10.1039/C5RA15342E	journal	January 2015
Site-selective ¹⁸ F fluorination of unactivated C–H bonds mediated by a manganese porphyrin Liu, Wei; Huang, Xiongyi; Placzek, Michael S. Chemical Science, Vol. 9, Issue 5 https://doi.org/10.1039/C7SC04545J	journal	January 2018
Synthesis and PET imaging studies of [18F]2-fluoroquinolin-8-ol ([18F]CABS13) in transgenic mouse models of Alzheimer's disease Vasdev, Neil; Cao, Pengpeng; van Oosten, Erik M. MedChemComm, Vol. 3, Issue 10 https://doi.org/10.1039/c2md20075a	journal	January 2012
Oxidative Aliphatic C-H Fluorination with Fluoride Ion Catalyzed by a Manganese Porphyrin Liu, W.; Huang, X.; Cheng, M. -J. Science, Vol. 337, Issue 6100 https://doi.org/10.1126/science.1222327	journal	September 2012
18F-Labeled 2-Arylquinoline Derivatives for Tau Imaging: Chemical, Radiochemical, Biological and Clinical Features Furumoto, Shozo; Tago, Tetsuro; Harada, Ryuichi Current Alzheimer Research, Vol. 14, Issue 2 https://doi.org/10.2174/1567205013666160620121811	journal	January 2017
Review of 18F-FDG synthesis and quality control Yu, S. Biomedical Imaging and Intervention Journal, Vol. 2, Issue 4 https://doi.org/10.2349/biij.2.4.e57	journal	January 2006

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Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups Li, Xiaowei; Shi, Xiaolin; Li, Xiangqian Beilstein Journal of Organic Chemistry, Vol. 15 https://doi.org/10.3762/bjoc.15.218	journal	January 2019
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